Donald Trump and Vladimir Putin have a history of bizarre encounters.

There was the pair’s first meeting in Germany when Trump confiscated his interpreter’s notes to conceal any evidence of what had happened in the room. The time in Vietnam where Trump took at face value Putin’s insistence that Moscow had not meddled in the 2016 election. And their summit in Helsinki when Trump questioned the analysis of his own intelligence services given Putin’s strong denial.

Now, as the two leaders prepare for their first face-to-face meeting since Trump returned to the White House, policymakers and analysts are braced for an unconventional meeting that will showcase a less encumbered Trump than he was in his first term.

Many fear that if these previous encounters are any indication, it is Putin, the seasoned KGB operative turned strongman, who will gain the upper hand — not the other way around.

“There is no way you can go from no progress to a summit that ends the war in less than a week,” said Samuel Charap, a senior political scientist at the Rand Corporation. “But Trump has this undying belief in his own charisma and ability to persuade his counterparts in what he thinks is logical and right.”

Vladimir Putin offers a ball of the 2018 football World Cup to President Donald TrumpAfter their meeting in Helsinki in 2018, Donald Trump questioned the analysis of his own intelligence team about Vladimir Putin © Yuri Kadobnov/AFP/Getty Images

Former French president François Hollande, who in 2015 co-led peace negotiations with then German Chancellor Angela Merkel and Putin over Ukraine, has a warning for the US president: “Putin’s technique is professional lying.”

“Trump would be well advised to show that he has detailed knowledge of the situation on the ground,” Hollande told the Financial Times.

When Trump and Putin met for the first time, in July 2017, the US leader was weighed down by the probe into alleged Russian election meddling and a mutual wariness between Trump and his own foreign policy advisers.

The two presidents huddled on the sidelines of a G20 summit in Hamburg, joined by Russia’s foreign minister and Trump’s then state secretary and two interpreters. Trump later took his interpreter’s notes and asked the interpreter not to brief anyone on the contents of the meeting.

Then at a dinner that night, Trump approached Putin for a one-on-one aside — with just Putin’s interpreter and no US officials present.

At their next meeting at the Asia-Pacific Economic Cooperation forum in Vietnam that November, Trump reiterated Putin’s claims that Russia had not interfered in the US election. 

The two had another face-to-face meeting in Helsinki in July 2018 where they were joined only by their respective interpreters. When asked at a news conference whether he believed his own intelligence agencies or the Russian president, Trump said he trusted both but noted: “President Putin says it’s not Russia. I don’t see any reason why it would be.”

The two men met again, informally, on the sidelines of the G20 summit in Buenos Aires later that year, where Trump again did not take any interpreter or note-taker with him.

This week’s summit represents the latest chance for Trump to once again recast his relationship with Putin and adopt a harsher stance on the Russian president. Few expect he will take the opportunity.

“Putin will try to convince Trump that [the Russian] position is better than it actually is. While for Trump it is much more important to make this deal and to claim it [as] his new peacekeeping victory,” said Kirill Rogov, a sociologist and visiting fellow at the Institute for Human Sciences in Vienna. “It ends in nothing, but Trump avoids the need to take decisive action.”

Hollande, who spent 17 hours in the capital of Belarus in February 2015 to seal the so-called Minsk 2 accord on a ceasefire in the eastern Ukrainian region of Donbas, said that Putin will probably play for time.

Russian President Vladimir Putin, former French President François Hollande, then-German chancellor Angela Merkel and former Ukrainian President, Petro PoroshenkoFormer French president François Hollande and then-German chancellor Angela Merkel in 2015 co-led peace negotiations with Putin and then Ukrainian president, Petro Poroshenko, over Ukraine © Mykola Lazarenko/AP

“He’s in no hurry,” the former French president said. “He knows that he will still be in power in a month, two years, maybe until the end of his life. Trump is in a hurry because he has pledged to resolve all the world’s conflicts and wants results.”

Lengthy digressions were also a pattern, Hollande recalled. “Putin is going to start the meeting by retelling the whole story. It could last an hour, longer, if you don’t cut him off. The Russian method of negotiation is that it should last a long time but that nothing much happens,” he said.

“But in the end, he would always offer an opening — a mediation, another meeting, a working group — so that the other side could say, see, Putin has shifted a little.”

Enunciating plain lies was also one of the Russian leader’s tricks, Hollande said. For instance Putin insisted he had no contact with the pro-Russian separatists in eastern Ukraine, despite funding and supporting them militarily. “It was such a big lie that it was impressive,” Hollande said.

A German diplomat involved in the Minsk negotiations described Putin as “one of the most skilled negotiators”. “He knows all the subjects, legal reasoning in details, but always manipulates facts. You have to know your facts as well as he does.”

But facts are not Trump’s forte, he said. In early 2017, Merkel arranged a call with the US president to explain how Putin was refusing to implement the Minsk accord. Trump just said thank you and hung up. Later US advisers told Merkel’s team that Trump was furious because she had lectured him. “Not only he doesn’t love facts, but he also has his prejudices, and Putin knows that,” the diplomat said.

In her memoirs, Merkel writes that she and Trump “were talking on two different levels: Trump on the emotional; I on the factual.”

Putin has a “very structured, very meticulous bad faith,” said a former French adviser in Hollande’s negotiating team. When the Russian leader refused to accept any external monitoring of the Ukrainian-Russian border, he “claimed it was not violated”, the adviser said. “But of course it’s because the Russians crossed it whenever they liked.”

Of the Alaska meeting, the adviser said: “The Russians are not going to strike a deal. Putin just needs Trump to stop supporting Ukraine, which is Trump’s natural inclination anyway.”

Rogov, the sociologist, said that Putin might be interested in negotiations more than before as the Russian summer offensive in Ukraine had been less successful than last year’s. The prospect of Trump scaring India off as an oil customer with the threat of tariffs further twisted Putin’s arm, he added.

Compared with his first administration, when Trump was constrained by an assertive Congress and by officials who sought to place guardrails on his relationship with Putin, the US president now faces fewer checks on his power. Republican lawmakers are cowed and the foreign policy apparatus has been sidelined.

“He is unconstrained,” said a senior US official, who spoke on condition of anonymity.

Trump and Steve Witkoff, his special envoy, have been running the operation like two “desk hands”, said Andrew Weiss, vice-president at the Carnegie Endowment for International Peace.

“We now have Trump without guardrails or counterweights in his own administration sitting with Putin, who has been in that position for a decade or so of not having peers in his own immediate proximity,” Weiss said.